Azo dyestuffs



Patented Dec. 30, 1941 UNITED STATES PATENT OFFICE AZO DYESTUFFS Werner Zerweck and Wilhelm Kunze, Frankforton-the-Main-Fechenheim, Germany, assignors to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application April 19, 1940, Serial No. 330,530. In Germany May 4, 1939 4 Claims.

This invention relates to am dyestuffs, more particularly to those of the general formula:

wherein aryl means a radicle of the benzene series, and the X8 have the aforesaid signification with coupling components which contain no substituents causing solubility in water.

The new dyestuffs are especially useful for dyeing and printing acetate artificial silk, and the dyeings and printings thus obtained exhibit good fastness properties, particularly a good fastness to light.

By selecting the components in such a manner that at least one free aliphatic hydroxyl group is present in the molecule either of the diazo or the coupling component, the dyestuffs thus formed are distinguished on account of their essentially better tinctorial power by the valuable property of being capable when mixed with a dispersing agent of being fixed on acetate artificial silk from a neutral bath. The addition of soap to the dyeing bath can be dispensed with in such a case. Thus even a compact tissue or a strongly twisted yarn is dyed thoroughly.

In order to further illustrate our invention the are diazotized in the usual manner. The clear diazo solution is then added to a hydrochloric acid solution of 20 parts of dihydroxyethyl-metatoluidine with the addition of sodium acetate. When the dyestufi formation is complete the dyestuff of the formula:

OHrCHzOH CH3 ore-onion is isolated and mixed with a dispersing agent. It dyes acetate artificial silk from a bath which only contains sodium sulfate but no soap, bright orange shades of good fastness.

Example 2 The diazo solution prepared from 24.5 parts of 4-aminophenylsulfoylacetdimethylamide is combined with a hydrochloric acid solution of 20 parts of dihydroxyethyl-meta-toluidine. After the addition of sodium acetate the formed dyestuff of the formula:

Example 3 When combining the diazocompound of 24.5 parts of 4-aminophenylsulfoylacetdime-thylamide with a hydrochloric acid solution of 15.5 parts of diethylaniline and isolating the formed dyestuff after the addition of sodium acetate it may be mixed with a dispersing agent. It corre- CHzCHzOH HaC following examples are given, the parts being by sponds with the formula:

HaC

weight and all temperatures in degrees centigrade.

Escample 1 and dyes acetate artificial silk from a soap containing bath orange shades of good fastness.

When starting from 3-aminophenylsulfoylacetdimethylamide the formed dyestuff dyes reddish 21.4 parts of 4-aminophenyl-sulfoylacetamide yellow shades.

. diazo component the diazocompound of 30 parts 29 Example 4 ries, R means the radical of a member of the class 2537 parts of 4 aminophenylsulfoylacethydrox consisting of aniline and toluidine derivatives beyethylamide are diazotized and the diazosolution mg Substltllted at the o en atoms by a memthus obtained is combined with a hydrochloric of the class co sist g o alkyl and hydroxyacid solution of 15.5 parts of diethylaniline. alkyl groups a t X Sta for member of After the addition of sodium acetate the formed the group consisting of hydrogen, alkyl and hydyestufi of the formula: droxyalkyl, which dyestuifs are especially useful 11001120112 CHa-CHs is isolated and mixed with a dispersing agent. for dyeing and printing acetate artificial silk It dyes from a sodiumsulfate containing bath acefast shades.

tate artificial silk strong reddish orange shades 2. The .azo dyestufi of the formula:

of good fastness to water and washing even HRC CH CH strongly twisted dyed good being dyed thorough- I 2 3 1y therewith. n-oo-om-smOnmQ-w A similar dyestuff is obtained when using as H CHZOHa which dyestufi dyes acetate artificial silk from a of 4-aminophenylsulfoylacetdihydroxyethylamsoap containing bath orange shades of good fastide.

Example 5 H955- 3. The azo dyestuff of the formula:

The diazosolution, prepared from 29.2 parts of 25 3-chloro-4-aminophenylsulfoylacethydroxyethyl- HO CHZOH E amide is combined with a hydrochloric acid solu- N-oo-Cm-s0l-O O tion of 16.5 parts of hydroXyethylmeth'yl-meta- HrCHa toluidine and the formed dyestufi is isolated after the addition of sodiumacetate and mixed with a no which dyestuff dyes from a sodiumsulfate condispersing agent. The dyestufi thus obtained taining bath acetate artificial silk strong reddish of the formula: orange shades of good fastness to water and dyes acetate artificial silk from a sodium sulfate washing even strongly twisted dyed good being containing bath bright scarlet shades of a good dyed thoroughly therewith.

fastness to water, washing and light. 40 4. The azo dyestufi of the formula:

Similar valuable dyestufis are obtainedwhen HOOHTCHz CHzCHzOH using as coupling component diethylaniline or as l I diazo component the diazocompound of 3-chlorolTI'COCHTSOZQNZN 4-amino-phenylsulfoylacetdihydroxyethylamide H 01 CH3 CH1 v or of 2 chloro 4 ammophenylsulfoylacethydroxy which dyestuif dyes acetate artificial silk from a gi g fi' sodium sulfate containing bath bright scarlet 1 Azo dystuffs of the general formula, shades of a good fastness to water, washing and light.

WERNER ZERWECK. NO Calkyl0;Sary1-N=NR WILHELM KUNZE. X:

wherein aryl means a radicle of the benzene se- 

